This is completely cool and could only be enhanced by a young Sophia Loren riding shoot gun. While I have not had the opportunity to tour Italy by car, I have done Spain and recommend it highly.
Editor ITKT

New York – July 2, 2008: In what seems to be an impossible feat, Italy by Vintage Car has created a completely new way to see Italy – from behind the wheel of an authentic Italian vintage car. The vacation of a bygone era has returned. There is no better way to see Italy than from the front seat of an Alfa Romeo Spider or Lancia Aurelia.

Italy by Vintage Car Tours Italy by Vintage Car offers ultra-luxurious excursions through the most attractive regions of Italy with participants driving themselves in vintage Italian cars from the 1950s, 1960s and 1970s. The trips include stays at some of the very finest country hotels, dinners at extraordinary restaurants and the chance to travel way off the beaten track through the Italian countryside. Guests are free to travel at their own pace and trips are accompanied by a mechanic who washes and gasses the car each night, and makes any technical adjustments. Luggage is transported separately between hotels and will be waiting in the room when guests arrive.

Italy by Vintage Car offers four extended itineraries, the Best of Tuscany, the Amalfi Coast, Rome to Milan, Tuscany with Kids and a 3-day trip to Italy’s Lazio and Abruzzo regions – as well as custom tours.

Italy by Vintage Car Tours The owners of Italy by Vintage Car have years of expertise in touring and countless personal connections, offering their travelers access to people and places that the average traveler could only dream of. It all began when three girlfriends combined their love for Italy, vintage cars and organizing luxury vacations.

All Italy by Vintage Car trips include accommodations in deluxe hotels, many meals, snacks and tastings along the routes. Transfers from/to the starting point and from finish point, professional English-speaking guides for cultural visits, entrance fees, full-day use of vintage cars with unlimited mileage, full insurance (civil liability, driver and passenger, damage to car), gasoline and highway tolls, separate luggage transfers, emergency cell phone in the car, detailed maps and route suggestions, professional VCT Tour manager throughout the trip, additional vintage car and a support vehicle with mechanical assistance throughout and gratuities for porters and hotel service.